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N‐Propargyl tryptamines bearing N‐substituents such as propargyl, allyl, alkyl or benzyl groups undergo regioselective gold‐catalyzed cyclizations to the corresponding spiroindolenines, while it was previously shown that N‐sulfonyl‐N‐propargyl tryptamines lead to achiral azepino[4,5‐b]indoles. An asymmetric approach to these spiroindolenines is disclosed using chiral gold complexes, leading to enantiomeric...
N‐Propargyl‐ and N‐homoallenyl‐2‐bromo‐β‐tryptamines undergo gold(I)‐catalyzed dearomatizing cyclizations to afford 2‐bromospiroindolenines that are in situ hydrolyzed to furnish spirooxindoles in a one‐pot process. Tryptophane derivatives (R2=CO2Et) led upon cyclization to chiral spirooxindoles in excellent diastereoselectivities.
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